The New York Yankees are standing at 57-48, still gazing at the playoffs. But a slide in recent weeks has wiped out their division lead, and they are six games down from first place. General Manager Brian Cashman has already made a move, acquiring third baseman Ryan McMahon from the Rockies in exchange for pitcher prospects Griffin Herring and Josh Grosz. The Yanks have also dealt pitcher Clayton Beeter and outfielder Browm Martinez for utility infielder Amed Rosario from the Nationals.

Still, a larger problem is emerging in the Bronx, one that could jeopardize their entire season.

That problem is the bullpen. Their bullpen cannot be trusted, with a horrifying 6.14 ERA in 66 July innings. This collapse has backed Cashman into a corner. “I would import… some relievers, because our bullpen is taxed,” he admitted. Important arms such as closer Devin Williams (4.70 ERA) and Jonathan Loáisiga (4.78 ERA) have struggled all season. Now, Cashman has pledged that it will be resolved. “We’re going to go to town. We are going to do everything we possibly can to improve ourselves.”

The team’s game plan for repairing this major gap has become clear, and it is a shockingly conservative one. MLB Network insider Jon Heyman reported, “The Yankees are buying,” Heyman wrote. “But they aren’t nearly as aggressive a buyer as we all imagined when they were forging an early and large division lead that’s long gone now.” 

The front office is already thinking about landing elite relief arms, as Jon Heyman wrote, “Their focus turns now to the bullpen, and they are eyeing the best of a shockingly excellent group of relievers potentially available. Ryan Helsley, Emmanuel Clase, Cade Smith, Mason Miller, Jhoan Duran, and David Bednar are just some of the many glossy names on a long roster of relievers out there.” But as Heyman analyzes, they need to upgrade: “But they must do it now without hindering 2026 and beyond.”

That means the front office might be refusing to move its two best prospects, who are seen as the future of the franchise. “They certainly aren’t dealing their nearly untouchable prospects—George Lombard Jr. or Spencer Jones—for a reliever,” Heyman confirmed. It guards the organization long-term but may not do enough to rescue a season already falling away.

As Heyman put it, “A sale isn’t happening. But Yankees decision-makers, having paid attention, aren’t exactly all in, either.”

So, with their top prospects off the table, the Yankees have no choice but to navigate through a complicated market to secure their next bullpen savior.

Evaluating a star-studded bullpen market

The trade market for relievers works in tiers, and the Yankees’ self-imposed rules make the biggest names all but unreachable.

The most glamorous top-tier features Cleveland’s Emmanuel Clase, who is perhaps the most valuable reliever in baseball. He is a dominant closer at an outrageous team-friendly rate through 2026, with club options for 2027 and 2028. As a result, the Guardians would ask for a package centered around Jones or Lombard Jr., making him off-limits for New York.

Other top arms like Minnesota’s Jhoan Duran and Oakland’s Mason Miller are in a similar position. Duran is controllable through 2027, but the Twins are seeking at least two top-100-caliber prospects in return. The Athletics are believed to have a similar asking price for Miller, who is controllable through 2029. The price on these young, elite arms is just too steep for a team guarding its prime assets.

In the next tier are high-impact arms with less control, such as St. Louis Cardinals’ two-time All-Star closer Ryan Helsley. He has a 3.00 ERA this season, but is a rental who will be a free agent. It wouldn’t cost a top prospect to get him, but it would represent a shift from the philosophy the team has established. The recent Ryan McMahon trade illustrated that the Yankees want players they can control for longer than just a few months, which seems to push Helsley off their radar.

That reality makes Pittsburgh All-Star closer David Bednar the most logical target. He’s had a good season with a 2.19 ERA and 1.13 WHIP. Most importantly, he is under team control for another full season (2026) via arbitration. The Yankees are said to be in consistent touch with the Pirates. But mixed reports on whether the Pirates are looking for hitting prospects or are focusing on Yankees’ pitcher Carlos Lagrange have muddied the negotiations.

The Yankees could consider reclamation projects if a star deal doesn’t materialize.

Another unexpected name is Pirates reliever Dennis Santana. The Yankees released Santana just last year, but he has thrived in Pittsburgh with a 1.42 ERA after altering his pitch mix. Acquiring him would be a low-cost risk, but it would also be a clear sign of desperation from the front office.

Do you have any speculations before the trade deadline hits?